Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4798-4807.DOI: 10.6023/cjoc202106044 Previous Articles     Next Articles



王玉超a,b, 刘晋彪a,*(), 邱观音生b,*(), 杨宇b, 周宏伟b,*()   

  1. a 江西理工大学材料冶金化学学部 江西赣州 341000
    b 嘉兴学院生物与化学工程学院 浙江嘉兴 314001
  • 收稿日期:2021-06-24 修回日期:2021-08-22 发布日期:2021-09-02
  • 通讯作者: 刘晋彪, 邱观音生, 周宏伟
  • 基金资助:
    国家自然科学基金(21772067); 国家自然科学基金(21762018); 国家自然科学基金(21961014); 江西省自然科学基金(20192BCBL23009); 江西省自然科学基金(20202BABL203005); 江西省青年井冈学者奖励计划资助项目

Metal-Free Selenizative spiro-Tricyclization of N-Hydroxylethyl-N-arylpropiolamides

Yuchao Wanga,b, Jinbiao Liua(), Guanyinsheng Qiub(), Yu Yangb, Hongwei Zhoub()   

  1. a Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, Ganzhou, Jiangxi 341000
    b College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001
  • Received:2021-06-24 Revised:2021-08-22 Published:2021-09-02
  • Contact: Jinbiao Liu, Guanyinsheng Qiu, Hongwei Zhou
  • Supported by:
    National Natural Science Foundation of China(21772067); National Natural Science Foundation of China(21762018); National Natural Science Foundation of China(21961014); Natural Science Foundation of Jiangxi Province(20192BCBL23009); Natural Science Foundation of Jiangxi Province(20202BABL203005); Youth Jinggang Scholars Program in Jiangxi Province

Facile ipso-cyclization and regioselective ortho-capture of N-hydroxylethyl-N-arylpropiolamides are reported for the synthesis of various selenium-containing benzo[b]pyrrolo[2,1-c][1,4]oxazin-3-ones. The reaction works well with high efficiency and broad reaction scope. In the process, it is believed that α-addition of the propiolamide, sequential ipso-cyclization of the aniline, and regioselective ortho-capture with a hydroxyl group are involved.

Key words: selenization, dearomatization, ipso-cyclization, N-hydroxylethyl-N-phenylpropiolamide